D-Phenylalanine (PAMDB000992)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000992
Identification
Name: D-Phenylalanine
Description:D-phenylalanine is a member of the chemical class known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Phenylalanine (abbreviated as Phe or F) is an alpha-amino acid with the formula C6H5CH2CH(NH2)COOH. This essential amino acid is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. Metabolic engineering can enhance phenylalanine production in Pseudomonas aeruginosa[PMID: 18080813] D-phenylalanine can be synthesized by glucose fermentation in Pseudomonas aeruginosa using metabolic engineering. DAHP synthase and chorismate mutase-prephenate dehydratase form a pathway where L-phenylalanine synthesis is deregulated and L-phenylalanine is converted into D-phenylalanine [Applied Biocatalysis in Specialty Chemicals and Pharmaceuticals, Chapter 5, p 65-75, Chapter DOI: 10.1021/bk-2001-0776.ch005]
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2R)-2-amino-3-phenylpropanoate
  • (2R)-2-amino-3-phenylpropanoic acid
  • (R)-2-Amino-3-phenylpropionate
  • (R)-2-Amino-3-phenylpropionic acid
  • D-α-amino-β-phenylpropionate
  • D-α-amino-β-phenylpropionic acid
  • D-a-amino-b-Phenylpropionate
  • D-a-amino-b-Phenylpropionic acid
  • D-alpha-Amino-beta-phenylpropionate
  • D-alpha-Amino-beta-phenylpropionic acid
  • D-b-Phenyl-a-alanine
  • D-b-Phenylalanine
  • D-beta-Phenyl-alpha-alanine
  • D-beta-Phenylalanine
  • D-α-amino-β-Phenylpropionate
  • D-α-amino-β-Phenylpropionic acid
  • D-β-Phenyl-α-alanine
  • D-β-Phenylalanine
  • DL-phnylalanine
  • DPN
  • P1751_SIGMA
  • Phenyl-D-Alanine
  • Phenylalanine
  • Phenylalanine D-form
  • Sabiden
Chemical Formula: C9H11NO2
Average Molecular Weight: 165.1891
Monoisotopic Molecular Weight: 165.078978601
InChI Key: COLNVLDHVKWLRT-UHFFFAOYSA-N
InChI:InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)
CAS number: 673-06-3
IUPAC Name:2-amino-3-phenylpropanoic acid
Traditional IUPAC Name: DL-phenylalanine
SMILES:NC(CC1=CC=CC=C1)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
Kingdom Organic compounds
Super ClassPhenylpropanoids and polyketides
Class Phenylpropanoic acids
Sub ClassNot Available
Direct Parent Phenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Aralkylamine
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Water Solubility:28.2 mg/mL at 16 oC [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.14 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.2ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.12 m3·mol-1ChemAxon
Polarizability17.2 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
D-Phenylalanine + Water + Acceptor <> Phenylpyruvic acid + Ammonia + Reduced acceptor
Phenylpyruvic acid + Ammonia + cytochrome c nitrite reductase <> D-Phenylalanine + Water + cytochrome c nitrite reductase
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xs-0900000000-ff1b3ddc479e70084786View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-fc318d4d3cde828334e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9400000000-866eeb88a50bd575fa09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-407406ada2082438a579View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-1900000000-347dc84ca7da32c5c176View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9600000000-a608d60e21d3beb49b12View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00dl-9300000000-4782928378caea601f9bView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16998
HMDB IDNot Available
Pubchem Compound ID71567
Kegg IDC02265
ChemSpider ID969
Wikipedia IDPhenylalanine
BioCyc IDCPD-216
EcoCyc IDCPD-216

Enzymes

Protein Details
• D-amino acid dehydrogenase small subunit
General function:
Involved in D-amino-acid dehydrogenase activity
Specific function:
Oxidative deamination of D-amino acids
Gene Name:
dadA
Locus Tag:
PA5304
Molecular weight:
47.1 kDa
Reactions
A D-amino acid + H(2)O + acceptor = a 2-oxo acid + NH(3) + reduced acceptor.

Transporters

Protein Details
• Uncharacterized amino-acid ABC transporter ATP-binding protein yecC
General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Locus Tag:
PA5152
Molecular weight:
28.4 kDa
Protein Details
• Aromatic amino acid transport protein AroP
General function:
Involved in transport
Specific function:
Permease that is involved in the transport across the cytoplasmic membrane of the aromatic amino acids (phenylalanine, tyrosine, and tryptophan)
Gene Name:
aroP
Locus Tag:
PA3000
Molecular weight:
51 kDa